My First Boyfriend

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The next day, while Tim was busy at work, I spent some girl time with Anna, telling her about how things were with Tim.

"So, you want him in you, like...in your ass?" she asked me, once the conversation had inevitably turned to our sex lives. Anna had two or three friends with benefits, and she had some pretty kinky stories about what she did some nights. I was envious; she was out getting tied up and spanked, and I hadn't even let my boyfriend fuck me properly.

"Yeah...I want him. Totally. Have you...have you ever had a guy in your ass?"

"Last night, Saturday night, and last Thursday night. I love it. It feels so different form having a cock in your pussy. I can't really describe it to you, but you'll have to trust me. It hurts like hell the first time though. I even stretched myself out with toys before my first time." She winced. "Hurts. Like. Hell. But then again, so did getting my pussy pounded the first time."

I nodded. It would hurt, but he would understand. And the second time, it would feel better, and the third time even better after that. "Can you help me find something extra sexy to wear? I have a plan in mind."

And what a plan it was. Step one was dying my hair a beautiful shade of red. With my pale skin, it looked a natural fit. Step two was buying a new dress, snug over my round ass, falling just to the bottom of the curve itself. It hugged my breasts as well, too snug for a bra. It did have a little room in the front, so I could go without panties if I wanted (all part of my plan). I felt so naughty. It was wonderful. I did my makeup, then drove down to the recruiting office. It was still pretty early, before lunch, so I had time to wait. After about twenty minutes, Tim was left alone in the office. I tossed my hair back a little bit, giving it a little bit of a wild look, before walking in.

"Can I help you, Miss?" he asked. My head was turned, so he couldn't get a good view of my face. I dropped my voice slightly, asking to use the restroom. He pointed me in the right direction, and I snuck past him. That was the hard part. In there, I was able to peel my panties off, a thong with a magic eight ball triangle saying "Signs point to yes." Curling them up in my hand, I walked out, hoping he was still alone. I was lucky. Before he had a chance to see me properly, I walked up and kissed him deeply. He stuttered, and as he did, I snuck the panties into his hand. Only then did I let him see who it was.

"Samantha! I didn't recognize you! God, you look amazing." He looked down at his hand, seeing what I had put there. Reading them, he grinned. "Tonight's the night?" he asked, even though I'm sure he knew the answer already.

I blushed. "I want it to be," I said, swallowing hard. He looked around for a minute, making sure that no one would see him neglecting his duties. Then, he leaned in and kissed me hard, his tongue forcing my lips open.

"Then tonight," he said, leaning in to whisper into my ear, "tonight, I am going to fuck my girlfriend for her very first time." He nipped my ear after he said that, making me shudder in anticipation.

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5 Comments
dougroundupdougroundupalmost 6 years ago
Dsyphoria

That was a beautiful story, hearing it from the emotional perspective of the transgendered coming of age.

It is so sad that so many transgendered have so much trouble accepting the acceptance of others.

It certainly seems as if it is now a whole new era and time for awareness and understanding of transgender and transexual persons in our society I am hopeful as we see more and more trans icons in pop culture that our society not only accepts it but that more and more people are able to embrace it, or even enjoy the benefits of being or being with someone regardless and or in addition to the variations that make them unique. There are so many levels and shades of personalities and spirits. It isint just howthe packaging is wrapped or the out self is presented to this physical world.

There is always different likes and dislikes of what each person finds attractive or unattractive. If you were to base it upon beauty and what you are intially attracted and what you find attractive.....well if you are like me you take notice of a sexy shapely woman that presents herself with poise and meticulous detail to the way she looks... (already painting myself into a corner) Anyways my point being is that there are so many very fine looking ladies of fashion that radiate sexiness and allure. So what about the plumbing or the sexual orientation ect... a sexy lady is a sexy lady is a sexy lady . I dont care (well actually I kinda do... but not like what is considered mainstream) what they work with or what others say.... its not their business. So many are stigmitized with is it a he or a she ..... fine is fine is fine.... I know I am attracted first and foremost into femininity. I love the finer details of the style.... I also know that I also find sexiness in the fem package sporting a package. This is where I started painting myself into the corner, I dont wish to objectify any peoples . But I just will say this... I do so wish many more within the trans community could would or somehow accept that others accept them or even desire them for their difference. Somehow theres a catch 22 with dysphoria and ones gender. But I just wish that more and more could enjoy being different and accept their penis and enjoy being a real woman and not have to worry if their sexual organ is external or internal and even be proud that some find it a desiriable trait of womanhood.

AnonymousAnonymousalmost 11 years ago
Good Read!

Only thing, how is she still cumming after hormone treatment? That's the only thing wrong here!

AnonymousAnonymousalmost 12 years ago
Nicely Written

I thought it was very well written, especially with her being a true transsexual and someday wanting the surgery like me. My only criticism is that the story shouldn't have had her boyfriend giving her head! I don't want my man to even touch me between my legs till I have my SRS and he wouldn't even if I begged him, either. But I love having him in my mouth or inside me. This writer makes me remember my first love and the innocence of it all. From some of the things I've read, I must be strange, because I just want to love and be loved by a kind, decent (and well hung!) guy. I don't want to be with ten guys a night, I want a relationship with one man. Call me boring or a prude. I don't care.

AnonymousAnonymousalmost 12 years ago

Very nicely written story. Nice character development. More please.

AnonymousAnonymousalmost 12 years ago
remembering

I remember my first,you bring back that wonderful memory,great story.

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